How do ring currents affect (1)h NMR chemical shifts?

Conventional explanations of proton NMR chemical shifts need fundamental revisions. Ab initio (IGLO) analyses reveal that the downfield delta (1)H of benzene is not due to deshielding ring current effects; the shielding is less than the pi contribution to vinyl delta (1)Hs. Enhanced deshielding sigm...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2003-03, Vol.5 (5), p.605-608
Hauptverfasser: Wannere, Chaitanya S, Schleyer, Paul Von Ragué
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Conventional explanations of proton NMR chemical shifts need fundamental revisions. Ab initio (IGLO) analyses reveal that the downfield delta (1)H of benzene is not due to deshielding ring current effects; the shielding is less than the pi contribution to vinyl delta (1)Hs. Enhanced deshielding sigma CC influences are responsible for the more downfield delta (1)Hs of the inner protons of naphthalene and anthracene. Double pi effects shield ethynyl Hs; there is no evidence for a special "ring current influence."
ISSN:1523-7060
DOI:10.1021/ol027327k